Chemistry of Anthracene–Acetylene Oligomers. X. Synthesis, Structures, and Properties of 1,8-Anthrylene–Alkynylene Cyclic Trimers

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  • Shinji Toyota
    Department of Chemistry, Faculty of Science, Okayama University of Science
  • Hiroaki Miyahara
    Department of Chemistry, Faculty of Science, Okayama University of Science
  • Michio Goichi
    Department of Chemistry, Faculty of Science, Okayama University of Science
  • Kan Wakamatsu
    Department of Chemistry, Faculty of Science, Okayama University of Science
  • Tetsuo Iwanaga
    Department of Chemistry, Faculty of Science, Okayama University of Science

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<jats:title>Abstract</jats:title> <jats:p>Two types of 1,8-anthrylene cyclic trimers with acetylene and diacetylene linkers were synthesized by macrocyclization of the acyclic precursors with Eglinton coupling as examples of the smallest analogues with an odd number of anthracene units. The X-ray analysis and DFT calculations revealed the nonplanar and strained cyclic structures of C2 and Cs symmetries for the compound with three diacetylene linkers and that with one diacetylene and two acetylene linkers, respectively, with significant bending deformations of acetylene carbons and anthracene moieties. The dynamic behavior of these cyclic compounds was analyzed by VT NMR measurements with the aid of DFT calculations. The NMR chemical shifts and the electronic spectra of the trimers are compared with those of the tetramers and dimers in terms of the orientation of anthracene units and the molecular strains.</jats:p>

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